US3117911A - Method of dyeing live human hair - Google Patents

Method of dyeing live human hair Download PDF

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Publication number
US3117911A
US3117911A US826454A US82645459A US3117911A US 3117911 A US3117911 A US 3117911A US 826454 A US826454 A US 826454A US 82645459 A US82645459 A US 82645459A US 3117911 A US3117911 A US 3117911A
Authority
US
United States
Prior art keywords
hair
dyeing
water
nitro
solution
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US826454A
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English (en)
Inventor
Kalopissis Gregoire
Bugaut Raymond
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by LOreal SA filed Critical LOreal SA
Priority to US146006A priority Critical patent/US3188346A/en
Application granted granted Critical
Publication of US3117911A publication Critical patent/US3117911A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/418—Amines containing nitro groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B51/00—Nitro or nitroso dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/30—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts

Definitions

  • nitroparaphenylenedia-mine as a product in the composition of dyeing solutions for hair or other keratinous fibres.
  • this dyestuti has the advantage that, on the one hand, it has a great afiinity in the cold for keratinous fibres, while on the other hand it can in some cases be readily eliminated, which is very advantageous when it is desired to effect only a temporary dyeing.
  • this dyestuff has the considerable disadvantage that only orange-red shades can be obtained therewith.
  • R represents an amino (-NH group or carboxymethylamino (-NHCH COOH) group.
  • the dyes thus defined when applied to human hair, are capable of giving shades verging upon blue-violet when the operation is carried out at an acid, neutral or alkaline pH, e.g., a pH from 2 to 9.
  • a process for the production of dyes of the general formula set forth above which comprises nitrating N-rnethylacetanilide by treatment with a rnixture of sulphui ic and nitric acids, reducing the 4-nitro-N-meth- "ice ylacetanilide thus obtained to the corresponding 4-amin0 compound, acetylating the said 4-amino compound, nitrating the product, subjecting the N-methyl-N-acetyl-N'- acetyl-meta-nitroparaphenylene-diamine thus obtained to deacetylation to produce 4-arnino-3-nitro-1-methylaminobenzene and, if desired, treating this product with monochloroacetic acid to produce 4-carboxymethylamino-3- nitro-l methylarninobenzene.
  • the product is neutralised with sodium carbonate, filtered, washed with boiling water and cooled, and there are added to the filtrate 500 g. of acetic anhydride. The mixture is maintained at 80 C. for about 30 minutes. After cooling, the product is neutralised with a caustic soda solution to a pH which is alkaline to phenolvphthalein.
  • the lock of hair is left in contact with the solution for 20 minutes at 20 C. It is then shampooed, rinsed with water and dried with Warm air. It is tinted an intense reddish violet.
  • the solution thus obtained has a pH of about 7.2.
  • the lock of hair is left in contact with the solution for 20 minutes at about 20 C. It is then shampooed, rinsed with water and dried with warm air (about -40 C.).
  • Lactic acid q.s. for pH 6.
  • Water q.s. for 10 cc.
  • the lock of hair is left in contact with the solution for 20 minutes at about 20 C. It is then shampooed, rinsed with Water and dried in the air.
  • the shade obtained is reddish violet.
  • the lock of hair is left in contact with the solution for 20 minutes at about 20 C. It is then shampooed, rinsed with Water and dried in the air.
  • the shade obtained is pink-beige.
  • the lock of hair is left in contact 'with the solution for 20 minutes at about 20 C. It is then shampooed, rinsed with water and dried in the air.
  • the shade obtained is blue-violet.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coloring (AREA)
US826454A 1959-04-23 1959-07-13 Method of dyeing live human hair Expired - Lifetime US3117911A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US146006A US3188346A (en) 1959-04-23 1961-10-18 4-amino-3-nitro methylamino-aniline and process for the preparation thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR792972A FR1253228A (fr) 1959-04-23 1959-04-23 Nouveaux produits utilisables pour la teinture des cheveux et autres fibres kératiniques et leur procédé de préparation

Publications (1)

Publication Number Publication Date
US3117911A true US3117911A (en) 1964-01-14

Family

ID=8714037

Family Applications (2)

Application Number Title Priority Date Filing Date
US826454A Expired - Lifetime US3117911A (en) 1959-04-23 1959-07-13 Method of dyeing live human hair
US412275A Expired - Lifetime US3291823A (en) 1959-04-23 1964-10-23 4-carboxymethylamino-3-nitro-1-methylaminobenzene as a dyeing agent

Family Applications After (1)

Application Number Title Priority Date Filing Date
US412275A Expired - Lifetime US3291823A (en) 1959-04-23 1964-10-23 4-carboxymethylamino-3-nitro-1-methylaminobenzene as a dyeing agent

Country Status (7)

Country Link
US (2) US3117911A (sv)
BE (1) BE589979A (sv)
CH (1) CH359242A (sv)
DE (1) DE1170583B (sv)
FR (1) FR1253228A (sv)
GB (1) GB867220A (sv)
NL (4) NL275277A (sv)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3271451A (en) * 1962-07-03 1966-09-06 Merck & Co Inc Process for preparing 5-(3-methylaminopropyl)-5h-dibenzo [a, d] cycloheptenes
US3658454A (en) * 1969-05-16 1972-04-25 American Cyanamid Co Dyeing keratinaceous material with n-carbamoylethyl amines
US4600797A (en) * 1979-10-23 1986-07-15 Bayer Aktiengesellschaft Process for the preparation of nitroaminobenzenes
US5685881A (en) * 1992-12-03 1997-11-11 Henkel Kommanditgesellschaft Auf Aktien Aromatic allylaminonitro compounds, hair dye compositions containing aromatic allylaminonitio compounds, and synthetic and natural fiber dyeing process

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1458155A (fr) * 1965-04-23 1966-03-04 Oreal Nouveaux dérivés nitrés acides
GB2086408B (en) * 1980-10-16 1985-10-09 Oreal New nitro-derivatives of the benzene series the process for their preparation and their use in the dyeing of keratin fibres
DE3543020A1 (de) * 1985-12-05 1987-06-11 Wella Ag Verfahren zur herstellung von 4-(ethyl-(2'hydroxyethyl)-amino)-1-((2'-hydroxyethyl)-amino)-2-nitro-benzol

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2580284A (en) * 1949-04-11 1951-12-25 Shell Dev Production of secondary aromatic amines
US2750326A (en) * 1951-02-07 1956-06-12 Lever Brothers Ltd Process and composition for dyeing hair
US2750327A (en) * 1953-06-01 1956-06-12 Lever Brothers Ltd Process of dyeing animal fibers and dyes and dyeing compositions therefor
US2814646A (en) * 1954-04-29 1957-11-26 Ethyl Corp Amine alkylation using aluminum anilide catalyst
US2889315A (en) * 1954-12-15 1959-06-02 Geigy Ag J R Water soluble dye salts and process for the production thereof
US2943109A (en) * 1957-05-27 1960-06-28 Ici Ltd Photographic developers

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1137929A (fr) * 1955-11-29 1957-06-05 Oreal Nouveau type de colorant et composition pour la teinture des cheveux

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2580284A (en) * 1949-04-11 1951-12-25 Shell Dev Production of secondary aromatic amines
US2750326A (en) * 1951-02-07 1956-06-12 Lever Brothers Ltd Process and composition for dyeing hair
US2750327A (en) * 1953-06-01 1956-06-12 Lever Brothers Ltd Process of dyeing animal fibers and dyes and dyeing compositions therefor
US2814646A (en) * 1954-04-29 1957-11-26 Ethyl Corp Amine alkylation using aluminum anilide catalyst
US2889315A (en) * 1954-12-15 1959-06-02 Geigy Ag J R Water soluble dye salts and process for the production thereof
US2943109A (en) * 1957-05-27 1960-06-28 Ici Ltd Photographic developers

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3271451A (en) * 1962-07-03 1966-09-06 Merck & Co Inc Process for preparing 5-(3-methylaminopropyl)-5h-dibenzo [a, d] cycloheptenes
US3658454A (en) * 1969-05-16 1972-04-25 American Cyanamid Co Dyeing keratinaceous material with n-carbamoylethyl amines
US4600797A (en) * 1979-10-23 1986-07-15 Bayer Aktiengesellschaft Process for the preparation of nitroaminobenzenes
US5685881A (en) * 1992-12-03 1997-11-11 Henkel Kommanditgesellschaft Auf Aktien Aromatic allylaminonitro compounds, hair dye compositions containing aromatic allylaminonitio compounds, and synthetic and natural fiber dyeing process

Also Published As

Publication number Publication date
NL102557C (sv)
NL275277A (sv)
CH359242A (fr) 1961-12-31
BE589979A (fr) 1960-08-16
FR1253228A (fr) 1961-02-10
NL105502C (sv)
US3291823A (en) 1966-12-13
GB867220A (en) 1961-05-03
NL240434A (sv)
DE1170583B (de) 1964-05-21

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